Benzyl Chloride → 4-Benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride

HRID 1856111Notes

Reaction equation

HRID 1856111 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5](=[S:18])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:3]1.[CH2:25]([Cl:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC=CC=1>[Cl-:32].[CH2:25]([S:18][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)=[CH:7][N+:2]([CH3:1])=[CH:3][C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 1812371-Methyl-3-phenyl-5-(3-(trifluoromethyl)phenyl)pyridine-4-thione

Product 1

HCID 233456984-Benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.0 g. of 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridinethione and 10 ml. of benzyl chloride in benzene was heated under reflux for 6 hours. The mixture was cooled and the benzene was removed in vacuo. The residue was put on a silica gel column in benzene and the column was flushed with benzene. The product was then removed from the column with denatured ethanol. The ethanol was removed and the residue was crystallized from ether yielding 0.7 g. of 4-benzylthio-1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)pyridinium chloride, m.p. 70°-73°.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureunder reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. customthe benzene was removed in vacuo
  5. customthe column was flushed with benzene
  6. customThe product was then removed from the column with denatured ethanol
  7. customThe ethanol was removed
  8. customthe residue was crystallized from ether yielding 0.7 g

Sources & evidence

ORD record
ord-2f4d672dd67d495aa6afbc790cc5bb57
Source dataset
uspto-grants-1980_08
Patent number
US04218238

Reaction notes

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